The following is a guest contribution from James Anderson of 

It can be intimidating to approach older women.

It’s even more convoluted when you add age difference to the mix. You’re not sure how to treat her and many guys get in their own way. They make mistakes meeting older women that ruin their chances.

Today, I’ll talk about the 8 most common mistakes younger guys make when approaching older women. Once you learn to avoid these mistakes, you’ll see that approaching older women isn’t as mysterious as it sounds. And the reward is worth the study – there are plenty of reasons why you should date older women.

Bonus: Get free access to my new course and learn the 5 conversation mistakes that put you in the friendzone.

1. He Talks About Age

Being able to talk to a woman and keep her interested can take some practice. Knowing what NOT to say is a huge part of that. Talking about her age is a mistake that can manifest in a variety of ways.

You might mention age in complementary ways, not realizing you’re insulting her. You tell her she looks beautiful for her age, or how much you love older women. It may seem like a good idea to crack jokes about her age to lighten the mood, unaware of her sensitivities.

You might tell her she reminds you of your aunt or another older woman you know. Or, you say she’s the most “sophisticated” woman you’ve ever met. It’s best to play it safe and avoid age altogether. At least until she brings it up, or you know her better. Her age isn’t the most interesting thing about her anyway, so it shouldn’t be the initial topic of conversation.

2. He Approaches Her Like He Would a Younger Woman

Most older women don’t react the same way to approaches you’d use on younger women. This isn’t like online dating where it’s a numbers game and you can blast out 50 messages in 10 minutes and find some success using the highest rated cougar dating sites. They’ve been dating longer, so they have more experience. They know what works and what doesn’t. They generally don’t go for pickup lines, sweet talking, or overt sexual advances. You can try paying for her drinks, but it won’t work as often as it would on a younger woman.

That’s why you’re approaching an older woman in the first place, isn’t it? You’d like to skip the drunken giggling and meet someone with class. So don’t confuse the situation by sending mixed signals. If you’re unsure how to approach her, let her take the lead. Say hello, smile, and see where the conversation goes.

3. He Tries Too Hard to Impress Her

Most women can tell when a guy is showing off or trying to impress her. An older woman can pick up on nonsense faster, and she’s not impressed by showy efforts. She’s been dating longer and has probably seen it all. She doesn’t care about your accounting skills or your cool new app. She wants to get to know you. Don’t pretend to be someone you’re not. She’ll see through it and lose interest.

The old advice about being yourself holds its merits. If you feel like you want to impress her, check yourself and ask a question instead. Women love to talk about themselves. Ask her about her passions, her goals, her hobbies, or anything you’d like to know about her. Don’t just make small talk, focus on topics of conversation that SHE would find interesting.

4. He Lets Insecurities Get in His Way

So you’re younger than she is. Who cares? Don’t waste your time asking why she’s interested in you, or whether she’s using you for your youth. You can keep making the most common excuses for yourself to not even try. Give her a chance to show you she’s interested in you for the right reasons. Spend time with her rather than allowing insecurities to stand in your way.

Be the confident, interesting guy that you know you can be. She’ll pick up on that and like you for the qualities that define you. If your self-esteem starts dropping, politely step away and regather yourself. Stand up straight, remind yourself of at least three things you do well, and jump back in.

5. He Has His Guard Up 

Older women don’t have time for childish games. They went through that phase and paid their dues. She doesn’t want to sift through a minefield of obscurity to get to know you. Approach her with an open mind and heart. That lets her know you see her for who she is and want to meet her on a level playing field. You’re in this for the same reasons she is, and you don’t have to make it difficult.

6. He Tries to Act Older Than He Is

Don’t attempt to veil your identity in any way. If she wants an older man, she’ll tell you to leave. Older women will see through your facade faster than you realize. Younger guys don’t know how an older guy acts because, well, he isn’t one. Be your genuine self. No matter what age that is. She’ll pick up on it, and you’ll leave a lasting impression on her.

7. He Treats Her Like a Fetish

Dating older women might be some people’s fetish, but it isn’t everyone’s. Usually, younger guys date older women because they want someone with maturity and interesting life experiences. No woman wants to be treated like an item on some guy’s bucket list. Besides, fetishes are a third date conversation. You wouldn’t mention your foot fetish until you’ve at least learned her middle name, right?

8. He Makes Age-Based Assumptions

You might be playing narratives in your mind about what she’s like. It could go one of two ways. Maybe she wants to hurry up and settle down. Marry and have kids before she’s too old. Or, maybe she’s looking for a fling. Perhaps you think that just because she is older she wouldn’t use a top cougar dating app to meet a younger guy.

These assumptions are unfair, and most likely nowhere near reality. They’re cliche at best, and obstructive to your happiness at worst. Instead of making conjectures, get to know her. Ask about her life and learn what her narrative actually is. Find out how you fit into it and if it’s right for you.

Older women were women first before they became “older women.” Fundamentally, they want to be treated as women. Instead of drawing attention to your differences, celebrate what you have in common. Speak with confidence and get to know her. If there’s a connection, secure a way to see her again.

Wrapping Up Common Mistakes Younger Guys Make When Approaching Older Women…

Dating an older woman can be one of the best experiences of your life. They offer many enticing qualities you may not find in a woman your age. So there’s incentive to making sure your approach goes well. By avoiding these common mistakes, you can walk away knowing you’ve done everything possible to maximize success.

James Anderson is the Head Writer and Content Director for, the most popular dating advice site for men interested in dating older women. Beyond Ages is dedicated to helping men improve their lives through successful dating and personal development. You can reach James on either @BeyondAges or on FaceBook.